Hydrochloric Acid → HCID 9827063, compound

HRID 1838410Notes

Reaction equation

HRID 1838410 reaction equation
O.N1CCCC1.C([O:10][C:11](=[O:44])[CH:12]([CH2:31][CH2:32][N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43])[N:13]([CH3:30])[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])C=C.Cl>O1CCOCC1>[CH3:30][N:13]([S:14]([C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:21][CH:22]=1)(=[O:15])=[O:16])[CH:12]([CH2:31][CH2:32][N:33]1[C:34](=[O:43])[C:35]2=[CH:42][CH:41]=[CH:40][CH:39]=[C:36]2[C:37]1=[O:38])[C:11]([OH:44])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 31268PyrrolidineHCID 18753515HCID 18753515, compound2×

Product 1

HCID 9827063HCID 9827063, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Water (1.75 ml), tetrakis(triphenylphosphine)palldium(0) (8.2 mg. 0.007 mmol) and pyrrolidine (0.45 ml, 5.3 mmol) were successively added to a solution of (±)-N-methyl-N-(4-phenoxybenzenesulfonyl)-2-(2-phthalimidoethyl)glycine allyl ester (1.88 g, 3.5 mmol), the product of (3) above, in dioxane (33 ml) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was acidified with hydrochloric acid (1N) and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crystalline residue was washed with diethyl ether to give the title compound (1.64 g, yield 94%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe crystalline residue was washed with diethyl ether

Sources & evidence

ORD record
ord-4ae1f278338e4541884fa079f8a585c8
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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